But the gang's real power came in the early 1970s when a transfer to the Boston FBI field office, South Boston native John Connolly, visited William Bulger, then a state senator and James "Whitey" Bulger's older brother, Martorano testified. Connolly asked William Bulger if there was anything he could do for him, Martorano testified, and the senator responded: "You could keep my brother out of a trouble, that would be helpful."
The FBI agent agreed to meet with Whitey Bulger, and the Winter Hill gang was apprised of the sit-down.
"We told him, 'Be a good listener. At all times be a good listener and never tell him anything,'"' Martorano said.
Martorano said that Connolly started to protect the Winter Hill gang almost immediately, warning them that a business owner they had tried to extort had gone to the FBI. After that, "We saw the value of the relationship," Martorano told the court.
To say thank you, Martorano said the gang gave Connolly a "2-carat diamond."
But Martorano insisted he had no idea that Bulger was giving Connolly much more than money and gifts: information on rival wiseguys
Martorano's testimony comes more than a decade after he cut a deal with the government to testify against Bulger. He has been a free man since 2007 and Bulger's defense attorney J.W. Carney tried to delay the trial by arguing that the hitman has continued his life a crime, a claim that was denied by prosecutors and dismissed by a federal judge.
Still, Carney insists that Martorano – and other government witnesses expected to testify against Bulger – are not credible because they pointed fingers at one another to avoid lengthy prison sentences. Bulger sidekick, Kevin Weeks, and Flemmi are also on the witness list.
Carney had especially harsh words for Martorano calling him "criminal psychopath."
"He would kill people almost randomly. He would kill people as easily as we would order a cup of coffee... The federal government was so desperate to have John Martorano testify ... they basically put their hands up in the air and said take anything you want," Carney said.
Martorano testified after cross-examination of Boston bookmaker Dick O'Brien, 84, who was one of two bookies who testified that they paid "rent" to Bulger to stay in business. He recounted Bulger telling one bookmaking agent who got out of line that he liked to "kill a**holes like him." James Katz, 73, also testified that people who didn't pay Bulger could "wind up in the hospital."
O'Brien, 84, said he was trained in the business by his father, but when he brought his daughter into the mobbed-up enterprise she had a nervous breakdown and had to be hospitalized.
The breakdown came after Flemmi warned O'Brien what happened to turncoats.
Before he went to the meeting with Flemmi, O'Brien told his daughter to go to the FBI in Miami rather than in Boston because he didn't trust the agents working in that field office.
"It really upset her. We were very close," O'Brien said.
Carney asked if he came home after that meeting in Florida, whether he was harmed. O'Brien answered, "By the good graces of John Martorano I wasn't."
Bulger, 83, is charged with a 32-count indictment that includes accusations that he committed or ordered 19 murders, including the killings of two women who were romantically involved with his underlings. Bulger's trial comes 18 years after he disappeared ahead of a federal indictment.
He was arrested in June 2011 at a Santa Monica apartment complex where Bulger and his longtime companion Catherine Greig lived for 16 years as Charlie and Carol Gasko strolling the California coastline and shopping on the Third Avenue Promenade. Carney accused the FBI of "pretending to look for him" during opening arguments last week.
The government called those accusations absurd.